Hispanic/Latinx communities remain an underserved population in terms of health and physical activity opportunities. The rise of sport specialization can jeopardize these opportunities. Understanding the appeal and welcomeness that minoritized populations feel toward sport and sport specialization culture can play an important role in health promotion and breaking down barriers that widen the gap on physical activity levels in Hispanic/Latinx communities. To date, these studies have not qualitatively investigated Hispanic/Latinx youth sport dyads (parent and child) and how sport specialization perceptions have affected their sport participation experiences. We used a qualitative interpretative phenomenological analysis to explore experiences of Hispanic/Latinx high school athletes. We engaged in semistructured interviews with 12 parent-child dyads. The following 3 interrelated themes emerged: (a) expectations of youth sport participation, (b) meeting expectations of youth sport participation, (c) and (mis)alignment of cultures. Dyads describe a negative youth sport experience when both cultures do not align because of the rise in sport specialization and pay-to-play culture. Findings indicate that dyads understand what is necessary to participate in organized sport and do this by methods that are rooted in their Hispanic/Latinx culture.